Dimethylformamide → HCID 23369665, compound

HRID 1900740Notes

Reaction equation

HRID 1900740 reaction equation
[N:1]([CH2:4][CH:5]1[O:17][C:16]2[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=2)NC(=O)C=[CH:9]3)[CH2:6]1)=[N+]=[N-].[H][H].[CH3:21][N:22](C)[CH:23]=[O:24]>[C].[Pd]>[NH2:1][CH2:4][CH:5]1[O:17][C:16]2=[C:15]3[C:21](=[CH:9][CH:8]=[C:7]2[CH2:6]1)[NH:22][C:23](=[O:24])[CH:13]=[CH:14]3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23369706HCID 23369706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23369665HCID 23369665, compound

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

The compound obtained in Example 158 (0.50 g, 2.06 mmol) dissolved in dimethylformamide (12 ml) was combined with 10% palladium-carbon (0.30 g), then stirred in the stream of hydrogen for 1.5 hour. From the reaction mixture, palladium-carbon was filtered off. The filtrate was condensed under reduced pressure, and purified by silica gel column chromatography (eluent; chloroform: ammonia=methanol 15:1). 0.33 g of the tile compound was obtained as pale yellow crystals (74.0%). They were recrystallized from a solvent mixture of chloroform--methanol--n-hexane to obtain pale yellow prisms of the title compound (mp.: 233°-236° C. (dec.)).

Workup

  1. filtrationFrom the reaction mixture, palladium-carbon was filtered off
  2. customcondensed under reduced pressure
  3. custompurified by silica gel column chromatography (eluent; chloroform: ammonia=methanol 15:1)

Sources & evidence

ORD record
ord-55717be9e6ff47d8b3bd80336ef546b5
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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